(Z)-methyl 4-(3-((5-(3,4-dichlorophenyl)furan-2-yl)methylene)-2-oxo-5-phenyl-2,3-dihydro-1H-pyrrol-1-yl)benzoate | 1191052-41-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-methyl 4-(3-((5-(3,4-dichlorophenyl)furan-2-yl)methylene)-2-oxo-5-phenyl-2,3-dihydro-1H-pyrrol-1-yl)benzoate
• 英文别名: methyl 4-[(3Z)-3-[[5-(3,4-dichlorophenyl)furan-2-yl]methylidene]-2-oxo-5-phenylpyrrol-1-yl]benzoate
• CAS: 1191052-41-1
• 化学式: C₂₉H₁₉Cl₂NO₄
• 分子量: 516.38
• InChiKey: XCWHXIFMHSIAFW-QNGOZBTKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  59.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-methyl 4-(3-((5-(3,4-dichlorophenyl)furan-2-yl)methylene)-2-oxo-5-phenyl-2,3-dihydro-1H-pyrrol-1-yl)benzoate 在 lithium iodide 作用下， 以 吡啶 为溶剂， 以93%的产率得到(Z)-4-(3-((5-(3,4-dichlorophenyl)furan-2-yl)methylene)-2-oxo-5-phenyl-2,3-dihydro-1H-pyrrol-1-yl)benzoic acid
  参考文献：
  名称：

  Investigation of N-Aryl-3-alkylidenepyrrolinones as Potential Niemann−Pick Type C Disease Therapeutics

  摘要：

  A five-step synthesis of an array of N-aryl-3-alkylidenepyrrolinones, which are potential Niemann-Pick type C (NPC) disease therapeutics, is described. The synthetic route allows for the production of analogues, including photoaffinity and biotinylated derivatives. Compound 1a increased esterification by acyl-coenzyme A:cholesteryl acyltransferase in NPC1 mutant cells. It also decreased LDL uptake and increased cholesterol efflux in both NPC1-deficient and normal cells.

  DOI：

  10.1021/jm900707n
• 作为产物：
  描述：

  methyl 4-(2-acetoxy-5-phenyl-1H-pyrrol-1-yl)benzoate 、 5-(3,4-二氯苯基)糠醛 在 sodium tetrahydroborate 、 sodium acetate 、 乙酸酐 作用下， 以 甲醇 为溶剂， 反应 2.33h， 以74%的产率得到(Z)-methyl 4-(3-((5-(3,4-dichlorophenyl)furan-2-yl)methylene)-2-oxo-5-phenyl-2,3-dihydro-1H-pyrrol-1-yl)benzoate
  参考文献：
  名称：

  Investigation of N-Aryl-3-alkylidenepyrrolinones as Potential Niemann−Pick Type C Disease Therapeutics

  摘要：

  A five-step synthesis of an array of N-aryl-3-alkylidenepyrrolinones, which are potential Niemann-Pick type C (NPC) disease therapeutics, is described. The synthetic route allows for the production of analogues, including photoaffinity and biotinylated derivatives. Compound 1a increased esterification by acyl-coenzyme A:cholesteryl acyltransferase in NPC1 mutant cells. It also decreased LDL uptake and increased cholesterol efflux in both NPC1-deficient and normal cells.

  DOI：

  10.1021/jm900707n

文献信息

• Investigation of <i>N</i>-Aryl-3-alkylidenepyrrolinones as Potential Niemann−Pick Type C Disease Therapeutics
  作者：Casey C. Cosner、John T. Markiewicz、Pauline Bourbon、Christopher J. Mariani、Olaf Wiest、Madalina Rujoi、Anton I. Rosenbaum、Amy Y. Huang、Frederick R. Maxfield、Paul Helquist

  DOI：10.1021/jm900707n

  日期：2009.10.22

  A five-step synthesis of an array of N-aryl-3-alkylidenepyrrolinones, which are potential Niemann-Pick type C (NPC) disease therapeutics, is described. The synthetic route allows for the production of analogues, including photoaffinity and biotinylated derivatives. Compound 1a increased esterification by acyl-coenzyme A:cholesteryl acyltransferase in NPC1 mutant cells. It also decreased LDL uptake and increased cholesterol efflux in both NPC1-deficient and normal cells.